Total synthesis of dysiherbaine

Makoto Sasaki, Nobuyuki Akiyama, Koichi Tsubone, Muneo Shoji, Masato Oikawa, Ryuichi Sakai

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

An efficient total synthesis of dysiherbaine, a potent and subtype-selective agonist for ionotropic glutamate receptors, has been achieved. An advanced key intermediate in the previous synthesis of neodysiherbaine A and its analogues was selected as the starting point, and cis-oriented amino alcohol functionality on the tetrahydropyran ring was installed by using an intramolecular SN2 cyclization of N-Boc-protected amino alcohol. The amino acid appendage was constructed by catalytic asymmetric hydrogenation of enamide ester.

Original languageEnglish
Pages (from-to)5697-5700
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number32
DOIs
Publication statusPublished - 2007 Aug 6

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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